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Jamaica Vacation Packages

Build your package with 2 more options

Jamaica Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $751, price is now $699 per person
$699
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.
Friendly owners and the property was amazing Beautiful garden, even in the fall Breakfast was delicious

Reviewed on Sep 25, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,653, price is now $1,380 per person
$1,380
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Great views

Reviewed on Sep 25, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $933, price is now $859 per person
$859
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
Nice hot tubs

Reviewed on Sep 25, 2026

Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts

4 out of 5
Price was $1,005, price is now $942 per person
$942
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.

Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
Price was $938, price is now $884 per person
$884
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this vacation home in Ludlow. Enjoy free parking, laundry facilities, and cable TV channels. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.

Reviewed on Jun 26, 2025

Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Price was $910, price is now $858 per person
$858
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall

Reviewed on Jul 19, 2026

White Loop Condo 2 Bedroom Condo

White Loop Condo 2 Bedroom Condo

3 out of 5
Price was $1,263, price is now $1,263 per person
$1,263
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this golf condo in Ludlow. Enjoy free WiFi, an in-room coffeemaker, and an indoor pool. Popular attractions Okemo Mountain Resort and Black Ridge Ski Lift are located nearby.

Jamaica Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $751, price is now $699 per person
$699
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,653, price is now $1,380 per person
$1,380
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $933, price is now $859 per person
$859
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts

4 out of 5
Clock Tower Base Area
Price was $1,005, price is now $942 per person
$942
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)